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- Title
Highly Efficient and Enzymatic Regioselective Undecylenoylation of Gastrodin in 2-Methyltetrahydrofuran-Containing Systems.
- Authors
Yang, Rongling; Liu, Xueming; Chen, Zhiyi; Yang, Chunying; Lin, Yaosheng; Wang, Siyuan
- Abstract
Highly efficient and regioselective acylation of pharmacologically interesting gastrodin with vinyl undecylenic acid has been firstly performed through an enzymatic approach. The highest catalytic activity and regioselectivity towards the acylation of 7′-hydroxyl of gastrodin was obtained with Pseudomonas cepacia lipase. In addition, it was observed the lipase displayed higher activity in the eco-friendly solvent 2-methyltetrahydrofuran-containing systems than in other organic solvents. In the co-solvent mixture of tetrahydrofuran and 2-methyltetrahydrofuran (3/1, v/v), the reaction rate was 60.6 mM/h, substrate conversion exceeded 99%, and 7′-regioselectivity was 93%. It was also interesting that the lipase-catalyzed acylation couldn’t be influenced by the benzylic alcohol in gastrodin. However, pseudomonas cepacia lipase displayed different regioselectivity towards gastrodin and arbutin.
- Subjects
ARBUTIN; ACYLATION; ENZYMATIC analysis; CHEMICAL reactions; BURKHOLDERIA cepacia; REGIOSELECTIVITY (Chemistry)
- Publication
PLoS ONE, 2014, Vol 9, Issue 10, p1
- ISSN
1932-6203
- Publication type
Article
- DOI
10.1371/journal.pone.0110342